2,5-Dimethoxytetrahydrofuran → HCID 14521576, compound

HRID 964481Notes

Reaction equation

HRID 964481 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.C[Si](C)(C)[O:12][C:13]([O:22][CH3:23])=[CH:14][C:15]([O:17][Si](C)(C)C)=[CH2:16].C([O-])(O)=O.[Na+]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:13]([CH:14]1[C:15](=[O:17])[CH2:16][CH:5]2[O:4][CH:3]1[CH2:7][CH2:6]2)([O:22][CH3:23])=[O:12]

Participants

6

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 534150304-Methoxy-2,2,8,8-tetramethyl-6-methylidene-3,7-dioxa-2,8-disilanon-4-ene

Product 1

HCID 14521576HCID 14521576, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To 2,5-dimethoxytetrahydrofuran (39.6 g, 0.3 mol) in CH2Cl2 (anhydrous, 200 mL) at -78° C. under nitrogen was added TiCl4 (66 mL, 0.6 mol). After stirring for 30 min, 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene, 2, (78 g, 0.3 mol) in CH2Cl2 (anhydrous, 400 mL) was added at a rate such that the internal temperature was maintained below -55° C. The mixture was stirred for 3 h. Saturated NaHCO3 was added until the mixture was neutral to pH paper. The aqueous layer was extracted with ether (3×1 L). The dried (MgSO4) combined organic layers were concentrated to dryness. The residue was purified by flash chromatography (20% EtOAc/hexanes) to afford 20.5 g (37%) of 3 as a light brown oil.

Workup

  1. temperaturewas maintained below -55° C
  2. stirringThe mixture was stirred for 3 h
  3. extractionThe aqueous layer was extracted with ether (3×1 L)
  4. dry with materialThe dried (MgSO4)
  5. concentrationwere concentrated to dryness
  6. customThe residue was purified by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e40c07a55033407a87afe09b160182af
Source dataset
uspto-grants-1998_06
Patent number
US05770180

Reaction notes

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